Shynkarenko P. Synthesis of 2H-1-benzopyran contained heterocycles based on recyclization of 2-iminocoumarine-3-carboxylic acid derivatives

Українська версія

Thesis for the degree of Candidate of Sciences (CSc)

State registration number

0412U006193

Applicant for

Specialization

  • 02.00.03 - Органічна хімія

25-10-2012

Specialized Academic Board

Д 64.051.14

V.N. Karazin Kharkiv National University

Essay

Investigation objects: 3-heterylsubstitueted 2-iminocoumarines and 3- heterylsubstitueted 2Н-pyrano[2,3-c]pyridine-2-imines derivatives with cycles: thieno[2,3-d]pyrimidin-4-one, quinazolin-4-(thi)one, 2,4-dihydro-[1,2,4]triazole-3-thione and 1,3,4-thiadiazole. Aim: develop synthetic methods of novel 3-heterylsubstitueted 2-iminocoumarines and their derivatives with cycles: thieno[2,3-d]pyrimidin-4-one, quinazolin-4-(thi)one, 2,4-dihydro-[1,2,4]triazole-3-thione and 1,3,4-thiadiazole, based on recyclization of 2-iminocoumarine-3-carboxylic acid nitriles and thioamides. Methods and apparatus: organic synthesis methods; chemical, physical and physicochemical methods of analysis of organic compounds (NMR spectroscopy, mass spectrometry, X-ray structure analysis, IR spectroscopy, thin layer chromatography, elemental analysis); quantum-chemical semiempirical calculation methods. Theoretical and practical results: 2-iminocoumarine-3-carboxylic acid derivatives possible usage in synthesis of wide line of 3-heterylsubstitueted 2-iminocoumarines and their derivatives that have great practical importance at new biological active compounds searches have been systematically investigated. A new effective approach and procedures of 3-heterylsubstitueted 2-iminocoumarines synthesis, based on recyclization of 2-iminocoumarine-3-carboxylic acid nitriles and thioamides by action of binucleophilic reagents (o-phenylendiamine, 2-aminothiophenol, carboxylic acids hydrazides, anthranylamide and thioanthranylthioamide, 2-aminothiophen-3-carboxamides, thiosemicarbazides) have been suggested and theoretically validated. Novelty: An efficient and novel approach of the synthesis of 3-heterylsubstitueted 2-iminocoumarines with cycles: thieno[2,3-d]pyrimidin-4-one, quinazolin-4-(thi)one, 2,4-dihydro-[1,2,4]triazole-3-thione and 1,3,4-thiadiazole, based on recyclization of 2-iminocoumarine-3-carboxylic acid nitriles and thioamides by action of binucleophilic reagents have been suggested and experimentally developed. Degree of implementation: no. Sphere (sector) of usage: Laboratories and departments of different educational and scientific organizations that conduct researches in related subject area, research-and-development centers that discover biological active compounds.

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